Thiochromanoylpyrazolone derivatives

ABSTRACT

Thiochromanoylpyrazolone derivatives of the formula I                    
     where: 
     A is an unsubstituted or substituted, saturated or unsaturated alkyl chain; 
     R 1  is cyano, thiocyanato, nitro, OR 4 , SR 5 , SOR 6 , S0 2 R 6 , ONR 6 NR 7 , ON═CR 6 R 8 , NR 9 R 10 , P(O)R 11 R 12 , P(S)R 11 R 12 , COR, CO 2 R 6 , unsubstituted or substituted phenyl or heterocyclyl; 
     R 2  is alkyl, haloalkyl, alkoxy or haloalkoxy; 
     R 3  is hydrogen, alkyl or halogen; 
     X is oxygen, sulfur, S═O, S(═O) 2 , CR 13 R 14 , C═O or C═NR 15 ; 
     m is 0, 1 or 2; 
     n is 0, 1, 2, 3 or 4; 
     R 16  is substituted pyrazol-4-yl-carbonyl or substituted (4,5-dihydro-5-oxo-pyrazol-4-yl)methylidene; 
     and their agriculturally useful salts; 
     Processes for preparing the thiochromanoylpyrazolone derivatives, compositions comprising them, and the use of these derivatives or of the compositions comprising them for controlling undesirable plants are described.

This application is a 371 of PCT/EP99/09346 filed Dec. 15, 1999.

The present invention relates to novel thiochromanoylpyrazolone derivatives of the formula I

where:

A is C₁-C₆-alkanediyl, C₂-C₆-alkenediyl, C₄-C₆-alkadienediyl or C₂-C₆-alkinediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl;

R¹ is cyano, thiocyanato, nitro, OR⁴, SR⁵, SOR⁶, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁸, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R³ is hydrogen, halogen or C₁-C₆-alkyl;

X is oxygen, sulfur, S═O, S(═O)₂, CR¹³R¹⁴, C═O or C═NR¹⁵;

m is 0, 1 or 2;

n is 0, 1, 2, 3 or 4;

R⁴, R⁵ are one of the radicals mentioned under R⁶;

are hydrogen, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, P(O)R¹¹R¹² or P(S)R¹¹R¹²;

are phenylcarbonyl, phenoxycarbonyl, phenyl-C₁-C₄-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C₁-C₄-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl and C₁-C₄-haloalkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where the phenyl and the heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R⁷ is hydrogen or C₁-C₆-alkyl;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, cyano or C₁-C₆-alkoxy;

R⁹ is one of the radicals mentioned under R⁴; is C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, aminocarbonyl, N—C₁-C₆-alkylaminocarbonyl or N,N-di-(C₁-C₆-alkyl)aminocarbonyl;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹¹, R¹² are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹³, R¹⁴ are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, N—C₁-C₆-alkylamino, N—C₁-C₆-haloalkylamino, N,N-(di-C₁-C₆-alkyl)amino, N—C₁-C₆-alkoxyamino, N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;

or

R¹³, R¹⁴ together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R¹⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R¹⁶ is a radical IIa or IIb,

where:

R¹⁷ is hydroxyl, mercapto, halogen, OR²⁰, SR²⁰, SOR²¹, SO₂R²¹, OSO₂R²¹, P(O)R²²R²³, OP(O)R²²R²³, P(S)R²²R²³, OP(S)R²²R²³, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R¹⁹ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio;

R²⁰ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di-(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, di-(C₁-C₆-alkyl)aminothiocarbonyl or C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl or heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₃-C₆-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl;

is phenyl, phenyl-C₁-C₆-alkyl, heterocyclyl or heterocyclyl-C₁-C₆-alkyl, where the phenyl and the heterocyclyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R²², R²³ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R²⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, amino, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁵ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

and its agriculturally useful salts.

Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.

WO 97/30993 and WO 97/09327 disclose dioxothiochroman derivatives which are linked to a substituted (5-hydroxypyrazol-4-yl)carbonyl radical. However, the herbicidal properties of the prior art compounds and their compatibility with crop plants are not entirely satisfactory. It is an object of the present invention to provide novel, biological, in particular herbicidally active, compounds having improved properties.

This object is achieved by the thiochromanoylpyrazolone derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. This invention provides both the pure enantiomers or diastereomers and mixtures thereof.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, where the type of salt is usually immaterial. In general, suitable salts are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not negatively affect the herbicidal activity of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where here, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid additions salts are primarily chloride, bromide, fluorine, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

In the case that R¹⁷=hydroxyl or mercapto {Y=O,S}, IIa also represents, in lieu, the tautomeric forms IIa′ and IIa″

and IIb also represents, in lieu, the tautomeric forms IIb′ and IIb″.

The organic molecular moieties mentioned for the substituents R¹-R²⁵ or as radicals on phenyl and heterocyclyl radicals are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N,N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N-alkylcarbonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, alkoxyiminoalkyl, phenylalkylcarbonyl, heterocyclylalkylcarbonyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl or alkynediyl moities can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl, and the alkyl moieties of phenyl-C₁-C₄-alkyl, heterocyclyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkylcarbonyl or heterocyclyl-C₁-C₄-alkylcarbonyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkoxy) -N—(C₁-C₆-alkyl) amino, N—(C₁-C₆-alkoxy) -N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl, (C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl, N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C₁-C₆-alkyl, heterocyclyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl, 1-bromoethyl, 1-chloroethyl, 1-iodoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

C₁-C₆-haloalkyl, and the haloalkyl moieties of N—C₁-C₆-haloalkylamino: (C₁-C₄-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;

C₁-C₆-alkoxy, and the alkoxy moieties of N—C₁-C₆-alkoxyamino, N—C₁-C₆-alkoxy-N—C₁-C₆-alkylamino, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)-aminocarbonyl and N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)-aminocarbonyl: C₁-C₄-alkoxy, as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2--dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3--dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy, as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;

C₁-C₆-alkylthio: and the alkylthio moieties of C₁-C₆-alkylthiocarbonyl: C₁-C₄-alkylthio, as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio, as mentioned above, and also, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;

C₁-C₄-alkylsulfinyl (C₁-C₄-alkyl-S(═O)—): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;

C₁-C₆-alkylsulfinyl: C₁-C₄-alkylsulfinyl radical, as mentioned above, and also pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁-C₄-haloalkylsulfinyl: C₁-C₄-alkylsulfinyl, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;

C₁-C₆-haloalkylsulfinyl: C₁-C₄-haloalkylsulfinyl, as mentioned above, and also 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—), for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl: C₁-C₄-alkylsulfonyl, as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-²-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;

C₁-C₆-haloalkylsulfonyl: C₁-C₄-haloalkylsulfonyl, as mentioned above, and also 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;

C₁-C₆-alkylamino, and the alkylamino radicals of N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)amino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;

di-(C₁-C₄-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di-(1-methylethyl) amino, N,N-dibutylamino, N,N-di-(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino, N,N-di-(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

di-(C₁-C₆-alkyl)amino: di-(C₁-C₄-alkyl)amino, as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;

C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;

C₁-C₆-alkylcarbonyl, and the alkylcarbonyl radicals of C₁-C₆-alkylcarbonylamino: C₁-C₄-alkylcarbonyl, as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;

C₁-C₄-haloalkylcarbonyl: a C₁-C₄-alkylcarbonyl radical as, mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;

C₁-C₆-haloalkylcarbonyl: a C₁-C₄-haloalkylcarbonyl radical as mentioned above, and also 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorohexylcarbonyl;

C₁-C₄-alkoxycarbonyl: for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;

C₁-C₆-alkoxycarbonyl: C₁-C₄-alkoxycarbonyl, as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2--ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl;

C₁-C₄-haloalkoxycarbonyl: a C₁-C₄-alkoxycarbonyl radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;

C₁-C₆-haloalkoxycarbonyl: a C₁-C₄-haloalkoxycarbonyl radical as mentioned above, and also 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;

(C₁-C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;

(C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;

(C₁-C₆-alkylamino)carbonyl: (C₁-C₄-alkylamino)carbonyl, as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;

di-(C₁-C₄-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di-(1-methylpropyl)aminocarbonyl, N,N-di-(2-methylpropyl)aminocarbonyl, N,N-di-(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;

di-(C₁-C₆-alkyl)aminocarbonyl: di-(C₁-C₄-alkyl)aminocarbonyl, as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-(2-methylbutyl)aminocarbonyl, N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl, N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methylpentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1-ethylbutyl)aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;

di-(C₁-C₆-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl, N,N-di-(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di-(1-methylpropyl)aminothiocarbonyl, N,N-di-(2-methylpropyl)aminothiocarbonyl, N,N-di-(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl, N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N-(1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(2-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylaminothiocarbonyl, N-(2-methylpropyl)-N-propylaminothiocarbonyl, N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-(1-methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methylpropyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1-methylbutyl)aminothiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-methylpentyl)aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyl, N-methyl-N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothiocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methylpentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;

C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl, which is substituted by C₁-C₄-alkoxy, as mentioned above, i.e. for example, for methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)-butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)-butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)-butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl;

C₁-C₄-alkoxy-C₁-C₄-alkoxy, and the alkoxyalkoxy moieties of C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl: C₁-C₄-alkoxy which is substituted by C₁-C₄-alkoxy, as mentioned above, i.e., for example, for methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;

C₃-C₆-alkenyl, and the alkenyl moieties of C₃-C₆-alkenylcarbonyl, C₃-C₆-alkenyloxy, C₃-C₆-alkenyloxycarbonyl-, C₃-C₆-alkenylaminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, 2-butene-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl, and the alkenyl moieties of C₂-C₆-alkenylcarbonyl, phenyl-C₂-C₆-alkenylcarbonyl and heterocyclyl-C₂-C₆-alkenylcarbonyl: C₃-C₆-alkenyl, as mentioned above, and also ethenyl;

C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;

C₃-C₆-alkynyl, and the alkynyl moieties of C₃-C₆-alkynylcarbonyl, C₃-C₆-alkynyloxy, C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;

C₂-C₆-alkynyl, and the alkynyl moieties of C₂-C₆-alkynylcarbonyl: (₃-C₆-alkynyl, as mentioned above, and also ethynyl;

C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

C₁-C₆-alkanediyl: methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane--1,3-diyl, butane-1,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl, 1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3-diyl, pentane-2,2-diyl, 1-methylbutane-1,1-diyl, 1-methylbutane-1,2-diyl, 1-methylbutane-1,3-diyl, 1-methylbutane-1,4-diyl, 2-methylbutane-1,1-diyl, 2-methylbutane-1,2-diyl, 2-methylbutane-1,3-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylpropane-1,1-diyl, 2,2-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,2-diyl, 2,3-dimethylpropane-1,3-diyl, 2,3-dimethylpropane-1,2-diyl, 1,3-dimethylpropane-1,3-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-1,3-diyl, hexane-1,4-diyl, hexane-1,5-diyl, hexane-1,6-diyl, hexane-2,5-diyl, 2-methylpentan-1,1-diyl, 1-methylpentane-1,2-diyl, 1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl, 1-methylpentane-1,5-diyl, 2-methylpentane-1,1-diyl, 2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl, 2-methylpentane-1,4-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl, 3-methylpentane-1,3-diyl, 3-methylpentane-1,4-diyl, 3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl, 1,1-dimethylbutane-1,3-diyl, 1,1-dimethylbutane-1,4-diyl, 1,2-dimethylbutane-1,1-diyl, 1,2-dimethylbutane-1,2-diyl, 1,2-dimethylbutane-1,3-diyl, 1,2-dimethylbutane-1,4-diyl, 1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl, 1,3-dimethylbutane-1,3-diyl, 1,3-dimethylbutane-1,4-diyl, 1-ethylbutane-1,1-diyl, 1-ethylbutane-1,2-diyl, 1-ethylbutane-1,3-diyl, 1-ethylbutane-1,4-diyl, 2-ethylbutane-1,1-diyl, 2-ethylbutane-1,2-diyl, 2-ethylbutane-1,3-diyl, 2-ethylbutane-1,4-diyl, 2-ethylbutane-2,3-diyl, 2,2-dimethylbutane-1,1-diyl, 2,2-dimethylbutane-1,3-diyl, 2,2-dimethylbutane-1,4-diyl, 1-isopropylpropane-1,1-diyl, 1-isopropylpropane-1,2-diyl, 1-isopropylpropane-1,3-diyl, 2-isopropylpropane-1,1-diyl, 2-isopropylpropane-1,2-diyl, 2-isopropylpropane-1,3-diyl, 1,2,3-trimethylpropane-1,1-diyl, 1,2,3-trimethylpropane-1,2-diyl or 1,2,3-trimethylpropane-1,3-diyl;

C₂-C₆-alkenediyl: ethene-1,1-diyl, ethene-1,2-diyl, 1-propene-1,1-diyl, 1-propene-1,2-diyl, 1-propene-1,3-diyl, 2-propene-1,1-diyl, 2-propene-1,2-diyl, 2-propene-1,3-diyl, 1-butene-1,1-diyl, 1-butene-1,2-diyl, 1-butene-1,3-diyl, 1-butene-1,4-diyl, 2-butene-1,1-diyl, 2-butene-1,2-diyl, 2-butene-1,3-diyl, 2-butene-1,4-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-methyl-1-propene-1,2-diyl, 1-methyl-1-propene-1,3-diyl, 1-methyl-2-propene-1,1-diyl, 1-methyl-2-propene-1,2-diyl, 1-methyl-2-propene-1,3-diyl, 2-methyl-1,1-propene-1,1-diyl, 2-methyl-1-propene-1,3-diyl, 3-butene-1,1-diyl, 3-butene-1,2-diyl, 3-butene-1,3-diyl, 3-butene-1,4-diyl, 1-penten-1,1-diyl, 1-penten-1,2-diyl, 1-penten-1,3-diyl, 1-penten-1,4-diyl, 1-penten-1,5-diyl, 1-hexene-1,1-diyl, 1-hexene-1,2-diyl, 1-hexene-1,3-diyl, 1-hexene-1,4-diyl, 1-hexene-1,5-diyl or 1-hexene-1,6-diyl;

C₂-C₆-alkdienediyl: 1,3-butadiene-1,1-diyl, 1,3-butadiene-1,2-diyl, 1,3-butadiene-1,3-diyl, 1,3-butadiene-1,4-diyl, 1,3-pentadiene-1,1-diyl, 1,3-pentadiene-1,2-diyl, 1,3-pentadiene-1,3-diyl, 1,3-pentadiene-1,4-diyl, 1,3-pentadiene-1,5-diyl, 2,4-pentadiene-1,1-diyl, 2,4-pentadiene-1,2-diyl, 2,4-pentadiene-1,3-diyl, 2,4-pentadiene-1,4-diyl, 2,4-pentadiene-1,5-diyl, 1-methyl-1,3-butadiene-1,4-diyl, 1,3-hexadiene-1,1-diyl, 1,3-hexadiene-1,2-diyl, 1,3-hexadiene-1,3-diyl, 1,3-hexadiene-1,4-diyl, 1,3-hexadiene-1,5-diyl, 1,3-hexadiene-1,6-diyl, 1-methyl-1,3-pentadiene-1,2-diyl, 1-methyl-1,3-pentadiene-1,3-diyl, 1-methyl-1,3-pentadiene-1,4-diyl or 1-methyl-1,3-pentadiene-1,5-diyl;

C₂-C₆-alkynediyl: ethyne-1,2-diyl, 1-propyne-1,3-diyl, 2-propyne-1,1-diyl, 2-propyne-1,3-diyl, 1-butyne-1,3-diyl, 1-butyne-1,4-diyl, 2-butyne-1,1-diyl, 2-butyne-1,4-diyl, 1-methyl-2-propyne-1,1-diyl, 1-methyl-2-propyne-1,3-diyl, 1-pentyne-1,3-diyl, 1-pentyne-1,4-diyl, 1-pentyne-1,5-diyl, 2-pentyne-1,1-diyl, 2-pentyne-1,4-diyl, 2-pentyne-1,5-diyl, 3-pentyne-1,1-diyl, 3-pentyne-1,2-diyl, 3-pentyne-1,5-diyl, 4-pentyne-1,1-diyl, 4-pentyne-1,2-diyl, 4-pentyne-1,3-diyl, 4-pentyne-1,5-diyl, 1-hexyne-1,3-diyl, 1-hexyne-1,4-diyl, 1-hexyne-1,5-diyl, 1-hexyne-1,6-diyl, 2-hexyne-1,1-diyl, 2-hexyne-1,4-diyl, 2-hexyne-1,5-diyl, 2-hexyne-1,6-diyl, 3-hexyne-1,1-diyl, 3-hexyne-1,2-diyl, 3-hexyne-1,5-diyl, 3-hexyne-1,6-diyl, 4-hexyne-1,1-diyl, 4-hexyne-1,2-diyl, 4-hexyne-1,3-diyl, 4-hexyne-1,6-diyl, 5-hexyne-1,1-diyl, 5-hexyne-1,2-diyl, 5-hexyne-1,3-diyl, 5-hexyne-1,4-diyl or 5-hexyne-1,6-diyl;

C₃-C₆-cycloalkyl, and the cycloalkyl moieties of C₃-C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C₁-C₄-alkyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclyl-C₂-C₆-alkenylcarbonyl, heterocyclylcarbonyl-C₁-C₆-alkyl, N—(C₁-C₆-alkyl)-N-(heterocyclyl)aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered, C-bonded, heterocyclic ring which contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example, 5-membered rings with one heteroatom such as:

tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl,tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;

5-membered rings with two heteroatoms, such as tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl, Δ³-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;

5-membered rings with three heteroatoms, such as 1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl, 1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl, 1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl, 1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl, 1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl, 1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl, 1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl, 1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl, 1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl, 1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl, 1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl, 1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl, 1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;

5-membered rings with four heteroatoms, such as tetrazol-5-yl,

6-membered rings with one heteroatom, such as: tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;

6-membered rings with two heteroatoms, such as 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl, 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or Pyrazin-2-yl;

6-membered rings with three heteroatoms, such as 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl or

6-membered rings with four heteroatoms, such as 1,2,4,5-tetrazin-3-yl;

where the sulfur of the abovementioned heterocycles may be oxidized to give S═O or S(═O)₂;

and where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C₃-C₆-carbocycle or another 5- to 6-membered heterocycle.

N-bonded heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-bonded heterocyclic ring which contains at least one nitrogen and which may contain one to three identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, i.e., for example,

N-bonded 5-membered rings with one heteroatoms, such as: tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl or pyrrol-1-yl;

N-bonded 5-membered rings with two heteroatoms, such as tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl or imidazol-1-yl;

N-bonded 5-membered rings with three heteroatoms, such as 1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl, 1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl, 1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl, 1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl, 1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl, 1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl;

N-bonded 5-membered rings with four heteroatoms, such as tetrazol-1-yl;

and also N-bonded 6-membered rings with one heteroatom, such as:

piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl or 1,2-dihydropyridin-1-yl;

N-bonded 6-membered rings with two heteroatoms, such as hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5, 6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4, 5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;

and also N-bonded cyclic imides such as:

phthalimide, tetrahydrophthalimide, succinimide, maleinimide or glutarimide; 5-oxo-triazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or 2,4-dioxo-(1H, 3H)-pyrimidin-3-yl;

where, with a fused-on phenyl ring or with a C₃-C₆-carbocycle or a further 5- to 6-membered heterocycle, a bicyclic ring system may be formed.

All phenyl rings and heterocyclyl radicals, and all phenyl components in phenoxy, phenylalkyl, phenylcarbonylalkyl, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl or phenoxysulfonyl and heterocyclyl components in heterocyclyloxy, heterocyclylalkyl, heterocyclylcarbonylalkyl, heterocyclylcarbonyl, heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl are, unless stated otherwise, preferably unsubstituted, or they carry one to three halogen atoms and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.

The compounds of the formula I according to the invention where R¹⁶=IIa are referred to as compounds of the formula Ia, and compounds of the formula I where R¹⁶=IIb are referred to as Ib.

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case on their own or in combination:

A is C₁-C₆-alkanediyl or C₂-C₆-alkenediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl; preferably C₁-C₄-alkanediyl, such as methane-1,1-diyl, ethane-1,1-diyl or ethane-1,2-diyl, or C₂-C₄-alkenediyl, such as ethene-1,1-diyl, ethene-1,2-diyl, 1-methyl-ethene-1,2-diyl or 1-propene-1,2-diyl;

particularly preferably methane-1,1-diyl or ethene-1,2-diyl;

R¹ is cyano, thiocyanato, nitro, OR⁴, SR⁵, SOR⁶, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁸, NR⁹R^(10, P(O)R) ¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶ or N-bonded heterocyclyl, where the lastmentioned radical for its part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; preferably cyano, thiocyanato, nitro, OR⁴, SR⁵, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁷, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶ or N-bonded heterocyclyl, such as pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-1-yl, pyrrolidin-1-yl, tetrahydroisoxazol-2-yl or morpholin-4-yl; particularly preferably cyano, nitro, OR⁴, SO₂R⁶, ONR⁶R⁷, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶ or CO₂R⁶;

R² is C₁-C₄-alkyl, such as methyl, ethyl, propyl or 1-methylethyl;

R³ is hydrogen, halogen, such as fluorine, chlorine or bromine, or C₁-C₄-alkyl, such as methyl or ethyl; particularly preferably hydrogen, chlorine or methyl; very particularly preferably hydrogen;

X is S(═O)₂, CR¹³R¹⁴ or C═O; preferably S(═O)₂ or CR¹³R¹⁴;

m is 0, 1 or 2; preferably 2;

n is 0, 1, 2, 3 or 41; preferably 0,1 or 2; particularly preferably 0;

R⁴, R⁵ are one of the radicals mentioned under R⁶; are hydrogen, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, P(O)R¹¹R¹² or P(S)R¹¹R¹²; preferably C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkylsulfonyl;

R⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl and C₁-C₄-haloalkoxy-carbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

is preferably C₁-C₄-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy or C₁-C₄-alkoxycarbonyl;

R⁷ is hydrogen or C₁-C₄-alkyl, such as methyl or ethyl;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl or C₁-C₆-alkoxy; preferably hydrogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;

R⁹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₄-alkylcarbonyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or C₃-C₆-alkynyloxy;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹¹, R¹² are hydroxyl, C₁-C₆-alkyl or C₁-C₆-alkoxy;

R¹³, R¹⁴ are hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; preferably hydrogen or C₁-C₆-alkyl, such as methyl, ethyl or propyl;

or

R¹³, R¹⁴ together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

preferably (R¹³, R¹⁴) are hydrogen, C₁-C₄-alkyl such as methyl, ethyl or n-propyl or C₁-C₄-haloalkyl such as chloromethyl, fluoromethyl or trifluoromethyl; particularly preferably hydrogen, methyl or ethyl;

R¹⁷ is hydroxyl, mercapto, halogen, OR²⁰, SR²⁰, SOR²¹, SO₂R²¹, OSO₂R²¹, OP(O)R²²R²³, OP(S)R²²R²³, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

preferably hydroxyl, mercapto, halogen, OR²⁰, SR²⁰, SO₂R²¹, OSO₂R²¹, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹⁸ is hydrogen or C₁-C₄-alkyl, such as methyl, ethyl or propyl or 1-methylethyl;

preferably methyl, ethyl, propyl or 1-methylethyl;

particularly preferably methyl or ethyl;

R¹⁹ is hydrogen or C₁-C₄-alkyl, such as methyl, ethyl or propyl;

preferably hydrogen or methyl;

particularly preferably hydrogen;

R²⁰ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl, N,N-di(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)-N-(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl, di-(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocy-clylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxy-thiocarbonyl or heterocyclyl-C₁-C₆-alkenylcarbonyl, where the phenyl or the heterocyclyl radical of the 14 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

is preferably C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkyl-aminocarbonyl or N,N-di(C₁-C₆-alkyl)aminocarbonyl, where the abovementioned alkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio or C₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or the heterocyclyl radical of the 10 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-cycloalkyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where the phenyl or the heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R²², R²³ are hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R²⁴ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or di-(C₁-C₆-alkyl)amino, where the abovementioned alkyl, cycloalkyl or alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl;

is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R²⁵ is C₁-C₆-alkyl or C₃-C₆-alkenyl.

Very particularly preference is given to compounds of the formula I, where

R¹ is cyano, thiocyanato, nitro, OR⁴, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁷, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶ or N-bonded heterocyclyl;

R⁴ is C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, where the three abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl;

is C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, P(O)R¹R¹¹R¹² or P(S)R¹¹R¹²;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-(C-C₄-alkyl, where the phenyl and the heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl.

Very particular preference is also given to the compounds of the formula I, where

R¹ is cyano, thiocyanato, nitro, SR⁵, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁸, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, C₀ ₂R⁶ or N-bonded heterocyclyl.

Very particular preference is also given to the compounds of the formula I, where

R¹⁷ is hydroxyl.

Very particular preference is also given to the compounds of the formula I, where

R¹⁷ is halogen, OR²⁰, SR²⁰, SO₂R²¹, OSO₂R²¹, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

Likewise, very particular preference is given to the compounds of the formula I, where

R¹⁸ is C₁-C₄-alkyl;

R¹⁹ is hydrogen or C₁-C₄-alkyl.

Likewise, very particular preference is given to the compounds of the formula I, where

A is C₁-C₆-alkanediyl;

particularly preferably methanediyl;

R¹ is NO₂, OR⁴, SR⁵, SOR⁶, SO₂R⁶, NR⁹R¹⁰, P(O)R¹¹R¹² or N-bonded heterocyclyl;

particularly preferably OR⁴, SR⁵, SOR⁶, SO₂R⁶, P(O)R¹¹R¹² or N-bonded heterocyclyl;

with particular preference OR⁴, SR⁵, SOR⁶, SO₂R⁶, or P(O)R¹¹R¹²;

likewise with particular preference SR⁵ or SO₂R⁶;

likewise with particular preference OR⁴;

R³ is hydrogen;

X is CR¹³R¹⁴, C═O or SO₂;

particularly preferably CR¹³R¹⁴;

m is 2;

n is 0;

R⁴ is C₁-C₆-alkyl which may be partially or fully halogenated;

R⁵ is C₁-C₆-alkyl, C₃-C₆-alkenyl or heterocyclyl; particularly preferably C₁-C₆-alkyl or heterocyclyl; with particular preference C₁-C₆-alkyl;

R⁶ is C₁-C₆-alkyl which may be partially or fully halogenated; particularly preferably C₁-C₆-alkyl;

R⁹ is C₁-C₆-alkyl, C₃-C₆-alkenyl or C₁-C₄-haloalkylcarbonyl;

R¹⁰ is C₁-C₆-alkyl or C₃-C₆-alkenyl;

R¹¹,R¹² are C₁-C₆-alkyl;

R¹⁷ hydroxyl;

R¹⁸ is C₁-C₆-alkyl;

R¹⁹ is hydrogen or C₁-C₆-alkyl;

particularly preferably hydrogen.

Likewise, very particular preference is given to the compounds of the formula Ia.

Most preference is given to the compounds of the formula Ia (=I, where R³, R¹⁹=H, R¹⁷=OH, R¹⁸=CH₃, m=2, n═O), in particular to the compounds Ia1.1 to Ia1.285, where the radical definitions R¹ to R²³, A, X, m and n are of particular importance for the compounds according to the invention not only in combination with one another, but in each case also on their own.

TABLE 1 Ia1

No. A R¹ X Ia1.1 CH₂ NO₂ SO₂ Ia1.2 CH₂ OCH₃ SO₂ Ia1.3 CH₂ OCH₂CH₃ SO₂ Ia1.4 CH₂ O(CH₂)₂CH₃ SO₂ Ia1.5 CH₂ O(CH₂)₃CH₃ SO₂ Ia1.6 CH₂ OCH(CH₃)₂ SO₂ Ia1.7 CH₂ OCH(CH₃)CH₂CH₃ SO₂ Ia1.8 CH₂ OCH₂CH(CH₃)₂ SO₂ Ia1.9 CH₂ OC(CH₃)₃ SO₂ Ia1.10 CH₂ OCH₂CH═CH₂ SO₂ Ia1.11 CH₂ OCH₂CH═CH—CH₃ SO₂ Ia1.12 CH₂ OCH(CH₃)CH═CH₂ SO₂ Ia1.13 CH₂ OCH₂C≡CH SO₂ Ia1.14 CH₂ OCH(CH₃)C≡CH SO₂ Ia1.15 CH₂ OCH₂C≡C—CH₃ SO₂ Ia1.16 CH₂ OCH₂F SO₂ Ia1.17 CH₂ OCH₂Cl SO₂ Ia1.18 CH₂ OCF₃ SO₂ Ia1.19 CH₂ OCHF₂ SO₂ Ia1.20 CH₂ OCH₂CH₂F SO₂ Ia1.21 CH₂ OCH₂CH₂Cl SO₂ Ia1.22 CH₂ OCH₂CF₃ SO₂ Ia1.23 CH₂ OCH₂CCl₃ SO₂ Ia1.24 CH₂ OCH₂CN SO₂ Ia1.25 CH₂ OCH(CH₃)CN SO₂ Ia1.26 CH₂ OCH₂C₆H₅ SO₂ Ia1.27 CH₂ OCH₂(furan-2-yl) SO₂ Ia1.28 CH₂ OCH₂(furan-3-yl) SO₂ Ia1.29 CH₂ SCH₃ SO₂ Ia1.30 CH₂ SCH₂CH₃ SO₂ Ia1.31 CH₂ S(CH₂)₂CH₃ SO₂ Ia1.32 CH₂ S(CH₂)₃CH₃ SO₂ Ia1.33 CH₂ SCH(CH₃)₂ SO₂ Ia1.34 CH₂ SCH₂CH(CH₃)₂ SO₂ Ia1.35 CH₂ SCH₂CH═CH₂ SO₂ Ia1.36 CH₂ SCH₂C≡CH SO₂ Ia1.37 CH₂ SC₆H₅ SO₂ Ia1.38 CH₂ S(4-CH₃—C₆H₄) SO₂ Ia1.39 CH₂ S(4-Cl—C₆H₄) SO₂ Ia1.40 CH₂ SO₂CH₃ SO₂ Ia1.41 CH₂ SO₂CH₂CH₃ SO₂ Ia1.42 CH₂ SO₂(CH₂)₂CH₃ SO₂ Ia1.43 CH₂ SO₂(CH₂)₃CH₃ SO₂ Ia1.44 CH₂ SO₂CH(CH₃)₂ SO₂ Ia1.45 CH₂ SO₂CH₂CH(CH₃)₂ SO₂ Ia1.46 CH₂ SO₂CH₂CH═CH₂ SO₂ Ia1.47 CH₂ SO₂CH₂C≡CH SO₂ Ia1.48 CH₂ SO₂C₆H₅ SO₂ Ia1.49 CH₂ SO₂(4-CH₃—C₆H₄) SO₂ Ia1.50 CH₂ SO₂(4-Cl—C₆H₄) SO₂ Ia1.51 CH₂ SO₂CF₃ SO₂ Ia1.52 CH₂ N(OCH₃)CH₃ SO₂ Ia1.53 CH₂ P(O)(OCH₃)₂ SO₂ Ia1.54 CH₂ P(O)(OCH₂CH₃)₂ SO₂ Ia1.55 CH₂ P(O)(OC₆H₅)₂ SO₂ Ia1.56 CH₂ P(O)(CH₃)₂ SO₂ Ia1.57 CH₂ P(O)(CH₂CH₃)₂ SO₂ Ia1.58 CH₂ P(O)(C₆H₅)₂ SO₂ Ia1.59 CH₂ P(S)(OCH₃)₂ SO₂ Ia1.60 CH₂ P(S)(OCH₂CH₃)₂ SO₂ Ia1.61 CH₂ thien-2-yl SO₂ Ia1.62 CH₂ morpholin-4-yl SO₂ Ia1.63 CH₂ tetrahydroisoxazol-2-yl SO₂ Ia1.64 CH₂ pyrrolidin-1-yl SO₂ Ia1.65 CH₂ imidazol-1-yl SO₂ Ia1.66 CH₂ pyrazol-1-yl SO₂ Ia1.67 CH₂ 1,2,4-triazol-1-yl SO₂ Ia1.68 CH₂ NO₂ C(CH₃)₂ Ia1.69 CH₂ OCH₃ C(CH₃)₂ Ia1.70 CH₂ OCH₂CH₃ C(CH₃)₂ Ia1.71 CH₂ O(CH₂)₂CH₃ C(CH₃)₂ Ia1.72 CH₂ O(CH₂)₃CH₃ C(CH₃)₂ Ia1.73 CH₂ OCH(CH₃)₂ C(CH₃)₂ Ia1.74 CH₂ OCH(CH₃)CH₂CH₃ C(CH₃)₂ Ia1.75 CH₂ OCH₂CH(CH₃)₂ C(CH₃)₂ Ia1.76 CH₂ OC(CH₃)₃ C(CH₃)₂ Ia1.77 CH₂ OCH₂CH═CH₂ C(CH₃)₂ Ia1.78 CH₂ OCH₂CH═CH—CH₃ C(CH₃)₂ Ia1.79 CH₂ OCH(CH₃)CH═CH₂ C(CH₃)₂ Ia1.80 CH₂ OCH₂C≡CH C(CH₃)₂ Ia1.81 CH₂ OCH(CH₃)C≡CH C(CH₃)₂ Ia1.82 CH₂ OCH₂C≡C—CH₃ C(CH₃)₂ Ia1.83 CH₂ OCH₂F C(CH₃)₂ Ia1.84 CH₂ OCH₂Cl C(CH₃)₂ Ia1.85 CH₂ OCF₃ C(CH₃)₂ Ia1.86 CH₂ OCHF₂ C(CH₃)₂ Ia1.87 CH₂ OCH₂CH₂F C(CH₃)₂ Ia1.88 CH₂ OCH₂CH₂Cl C(CH₃)₂ Ia1.89 CH₂ OCH₂CF₃ C(CH₃)₂ Ia1.90 CH₂ OCH₂CCl₃ C(CH₃)₂ Ia1.91 CH₂ OCH₂CN C(CH₃)₂ Ia1.92 CH₂ OCH(CH₃)CN C(CH₃)₂ Ia1.93 CH₂ OCH₂C₆H₅ C(CH₃)₂ Ia1.94 CH₂ OCH₂(furan-2-yl) C(CH₃)₂ Ia1.95 CH₂ OCH₂(furan-3-yl) C(CH₃)₂ Ia1.96 CH₂ SCH₃ C(CH₃)₂ Ia1.97 CH₂ SCH₂CH₃ C(CH₃)₂ Ia1.98 CH₂ S(CH₂)₂CH₃ C(CH₃)₂ Ia1.99 CH₂ S(CH₂)₃CH₃ C(CH₃)₂ Ia1.100 CH₂ SCH(CH₃)₂ C(CH₃)₂ Ia1.101 CH₂ SCH₂CH(CH₃)₂ C(CH₃)₂ Ia1.102 CH₂ SCH₂CH═CH₂ C(CH₃)₂ Ia1.103 CH₂ SCH₂C≡CH C(CH₃)₂ Ia1.104 CH₂ SC₆H₅ C(CH₃)₂ Ia1.105 CH₂ S(4-CH₃—C₆H₄) C(CH₃)₂ Ia1.106 CH₂ S(4-Cl—C₆H₄) C(CH₃)₂ Ia1.107 CH₂ SO₂CH₃ C(CH₃)₂ Ia1.108 CH₂ SO₂CH₂CH₃ C(CH₃)₂ Ia1.109 CH₂ SO₂(CH₂)₂CH₃ C(CH₃)₂ Ia1.110 CH₂ SO₂(CH₂)₃CH₃ C(CH₃)₂ Ia1.111 CH₂ SO₂CH(CH₃)₂ C(CH₃)₂ Ia1.112 CH₂ SO₂CH₂CH(CH₃)₂ C(CH₃)₂ Ia1.113 CH₂ SO₂CH₂CH═CH₂ C(CH₃)₂ Ia1.114 CH₂ SO₂CH₂C≡CH C(CH₃)₂ Ia1.115 CH₂ SO₂C₆H₅ C(CH₃)₂ Ia1.116 CH₂ SO₂(4-CH₃—C₆H₄) C(CH₃)₂ Ia1.117 CH₂ SO₂(4-Cl—C₆H₄) C(CH₃)₂ Ia1.118 CH₂ SO₂CF₃ C(CH₃)₂ Ia1.119 CH₂ N(OCH₃)CH₃ C(CH₃)₂ Ia1.120 CH₂ P(O)(OCH₃)₂ C(CH₃)₂ Ia1.121 CH₂ P(O)(OCH₂CH₃)₂ C(CH₃)₂ Ia1.122 CH₂ P(O)(OC₆H₅)₂ C(CH₃)₂ Ia1.123 CH₂ P(O)(CH₃)₂ C(CH₃)₂ Ia1.124 CH₂ P(O)(CH₂CH₃)₂ C(CH₃)₂ Ia1.125 CH₂ P(O)(C₆H₅)₂ C(CH₃)₂ Ia1.126 CH₂ P(S)(OCH₃)₂ C(CH₃)₂ Ia1.127 CH₂ P(S)(OCH₂CH₃)₂ C(CH₃)₂ Ia1.128 CH₂ thien-2-yl C(CH₃)₂ Ia1.129 CH₂ morpholin-4-yl C(CH₃)₂ Ia1.130 CH₂ tetrahydroisoxazol-2-yl C(CH₃)₂ Ia1.131 CH₂ pyrrolidin-1-yl C(CH₃)₂ Ia1.132 CH₂ imidazol-1-yl C(CH₃)₂ Ia1.133 CH₂ pyrazol-1-yl C(CH₃)₂ Ia1.134 CH₂ 1,2,4-triazol-1-yl C(CH₃)₂ Ia1.135 CH₂ NO₂ C═O Ia1.136 CH₂ OCH₃ C═O Ia1.137 CH₂ OCH₂CH₃ C═O Ia1.138 CH₂ O(CH₂)₂CH₃ C═O Ia1.139 CH₂ O(CH₂)₃CH₃ C═O Ia1.140 CH₂ OCH(CH₃)₂ C═O Ia1.141 CH₂ OCH(CH₃)CH₂CH₃ C═O Ia1.142 CH₂ OCH₂CH(CH₃)₂ C═O Ia1.143 CH₂ OC(CH₃)₃ C═O Ia1.144 CH₂ OCH₂CH═CH₂ C═O Ia1.145 CH₂ OCH₂CH═CH—CH₃ C═O Ia1.146 CH₂ OCH(CH₃)CH═CH₂ C═O Ia1.147 CH₂ OCH₂C≡CH C═O Ia1.148 CH₂ OCH(CH₃)C≡CH C═O Ia1.149 CH₂ OCH₂C≡C—CH₃ C═O Ia1.150 CH₂ OCH₂F C═O Ia1.151 CH₂ OCH₂Cl C═O Ia1.152 CH₂ OCF₃ C═O Ia1.153 CH₂ OCHF₂ C═O Ia1.154 CH₂ OCH₂CH₂F C═O Ia1.155 CH₂ OCH₂CH₂Cl C═O Ia1.156 CH₂ OCH₂CF₃ C═O Ia1.157 CH₂ OCH₂CCl₃ C═O Ia1.158 CH₂ OCH₂CN C═O Ia1.159 CH₂ OCH(CH₃)CN C═O Ia1.160 CH₂ OCH₂C₆H₅ C═O Ia1.161 CH₂ OCH₂(furan-2-yl) C═O Ia1.162 CH₂ OCH₂(furan-3-yl) C═O Ia1.163 CH₂ SCH₃ C═O Ia1.164 CH₂ SCH₂CH₃ C═O Ia1.165 CH₂ S(CH₂)₂CH₃ C═O Ia1.166 CH₂ S(CH₂)₃CH₃ C═O Ia1.167 CH₂ SCH(CH₃)₂ C═O Ia1.168 CH₂ SCH₂CH(CH₃)₂ C═O Ia1.169 CH₂ SCH₂CH═CH₂ C═O Ia1.170 CH₂ SCH₂C≡CH C═O Ia1.171 CH₂ SC₆H₅ C═O Ia1.172 CH₂ S(4-CH₃—C₆H₄) C═O Ia1.173 CH₂ S(4-Cl—C₆H₄) C═O Ia1.174 CH₂ SO₂CH₃ C═O Ia1.175 CH₂ SO₂CH₂CH₃ C═O Ia1.176 CH₂ SO₂(CH₂)₂CH₃ C═O Ia1.177 CH₂ SO₂(CH₂)₃CH₃ C═O Ia1.178 CH₂ SO₂CH(CH₃)₂ C═O Ia1.179 CH₂ SO₂CH₂CH(CH₃)₂ C═O Ia1.180 CH₂ SO₂CH₂CH═CH₂ C═O Ia1.181 CH₂ SO₂CH₂C≡CH C═O Ia1.182 CH₂ SO₂C₆H₅ C═O Ia1.183 CH₂ SO₂(4-CH₃—C₆H₄) C═O Ia1.184 CH₂ SO₂(4-Cl—C₆H₄) C═O Ia1.185 CH₂ SO₂CF₃ C═O Ia1.186 CH₂ N(OCH₃)CH₃ C═O Ia1.187 CH₂ P(O)(OCH₃)₂ C═O Ia1.188 CH₂ P(O)(OCH₂CH₃)₂ C═O Ia1.189 CH₂ P(O)(OC₆H₅)₂ C═O Ia1.190 CH₂ P(O)(CH₃)₂ C═O Ia1.191 CH₂ P(O)(CH₂CH₃)₂ C═O Ia1.192 CH₂ P(O)(C₆H₅)₂ C═O Ia1.193 CH₂ P(S)(OCH₃)₂ C═O Ia1.194 CH₂ P(S)(OCH₂CH₃)₂ C═O Ia1.195 CH₂ thien-2-yl C═O Ia1.196 CH₂ morpholin-4-yl C═O Ia1.197 CH₂ tetrahydroisoxazol-2-yl C═O Ia1.198 CH₂ pyrrolidin-1-yl C═O Ia1.199 CH₂ imidazol-1-yl C═O Ia1.200 CH₂ pyrazol-1-yl C═O Ia1.201 CH₂ 1,2,4-triazol-1-yl C═O Ia1.202 CH═CH CN SO₂ Ia1.203 CH═CH NO₂ SO₂ Ia1.204 CH═CH SO₂CH₃ SO₂ Ia1.205 CH═CH SO₂CH₂CH₃ SO₂ Ia1.206 CH═CH SO₂(CH₂)₂CH₃ SO₂ Ia1.207 CH═CH SO₂(CH₂)₃CH₃ SO₂ Ia1.208 CH═CH SO₂CH(CH₃)₂ SO₂ Ia1.209 CH═CH SO₂CH₂CH(CH₃)₂ SO₂ Ia1.210 CH═CH COCH₃ SO₂ Ia1.211 CH═CH COCH₂CH₃ SO₂ Ia1.212 CH═CH COCH₂F SO₂ Ia1.213 CH═CH COCH₂Cl SO₂ Ia1.214 CH═CH COCH₂Br SO₂ Ia1.215 CH═CH COCF₃ SO₂ Ia1.216 CH═CH COCHF₂ SO₂ Ia1.217 CH═CH CO₂CH₃ SO₂ Ia1.218 CH═CH CO₂CH₂CH₃ SO₂ Ia1.219 CH═CH CO₂(CH)₂CH₃ SO₂ Ia1.220 CH═CH CO₂(CH₂)₃CH₃ SO₂ Ia1.221 CH═CH CO₂CH(CH₃)₂ SO₂ Ia1.222 CH═CH CO₂CH₂CH(CH₃)₂ SO₂ Ia1.223 CH═CH CO₂CH₂CH₂F SO₂ Ia1.224 CH═CH CO₂CH₂CH₂Cl SO₂ Ia1.225 CH═CH CO₂CH₂CF₃ SO₂ Ia1.226 CH═CH CO₂CH₂CCl₃ SO₂ Ia1.227 CH═CH CO₂C₆H₅ SO₂ Ia1.228 CH═CH furan-2-yl SO₂ Ia1.229 CH═CH thien-2-yl SO₂ Ia1.230 CH═CH CN C(CH₃)₂ Ia1.231 CH═CH NO₂ C(CH₃)₂ Ia1.232 CH═CH SO₂CH₃ C(CH₃)₂ Ia1.233 CH═CH SO₂CH₂CH₃ C(CH₃)₂ Ia1.234 CH═CH SO₂(CH₂)₂CH₃ C(CH₃)₂ Ia1.235 CH═CH SO₂(CH₂)₃CH₃ C(CH₃)₂ Ia1.236 CH═CH SO₂CH(CH₃)₂ C(CH₃)₂ Ia1.237 CH═CH SO₂CH₂CH(CH₃)₂ C(CH₃)₂ Ia1.238 CH═CH COCH₃ C(CH₃)₂ Ia1.239 CH═CH COCH₂CH₃ C(CH₃)₂ Ia1.240 CH═CH COCH₂F C(CH₃)₂ Ia1.241 CH═CH COCH₂Cl C(CH₃)₂ Ia1.242 CH═CH COCH₂Br C(CH₃)₂ Ia1.243 CH═CH COCF₃ C(CH₃)₂ Ia1.244 CH═CH COCHF₂ C(CH₃)₂ Ia1.245 CH═CH CO₂CH₃ C(CH₃)₂ Ia1.246 CH═CH CO₂CH₂CH₃ C(CH₃)₂ Ia1.247 CH═CH CO₂(CH)₂CH₃ C(CH₃)₂ Ia1.248 CH═CH CO₂(CH₂)₃CH₃ C(CH₃)₂ Ia1.249 CH═CH CO₂CH(CH₃)₂ C(CH₃)₂ Ia1.250 CH═CH CO₂CH₂CH(CH₃)₂ C(CH₃)₂ Ia1.251 CH═CH CO₂CH₂CH₂F C(CH₃)₂ Ia1.252 CH═CH CO₂CH₂CH₂Cl C(CH₃)₂ Ia1.253 CH═CH CO₂CH₂CF₃ C(CH₃)₂ Ia1.254 CH═CH CO₂CH₂CCl₃ C(CH₃)₂ Ia1.255 CH═CH CO₂C₆H₅ C(CH₃)₂ Ia1.256 CH═CH furan-2-yl C(CH₃)₂ Ia1.257 CH═CH thien-2-yl C(CH₃)₂ Ia1.258 CH═CH CN C═O Ia1.259 CH═CH NO₂ C═O Ia1.260 CH═CH SO₂CH₃ C═O Ia1.261 CH═CH SO₂CH₂CH₃ C═O Ia1.262 CH═CH SO₂(CH₂)₂CH₃ C═O Ia1.263 CH═CH SO₂(CH₂)₃CH₃ C═O Ia1.264 CH═CH SO₂CH(CH₃)₂ C═O Ia1.265 CH═CH SO₂CH₂CH(CH₃)₂ C═O Ia1.266 CH═CH COCH₃ C═O Ia1.267 CH═CH COCH₂CH₃ C═O Ia1.268 CH═CH COCH₂F C═O Ia1.269 CH═CH COCH₂Cl C═O Ia1.270 CH═CH COCH₂Br C═O Ia1.271 CH═CH COCF₃ C═O Ia1.272 CH═CH COCHF₂ C═O Ia1.273 CH═CH CO₂CH₃ C═O Ia1.274 CH═CH CO₂CH₂CH₃ C═O Ia1.275 CH═CH CO₂(CH)₂CH₃ C═O Ia1.276 CH═CH CO₂(CH₂)₃CH₃ C═O Ia1.277 CH═CH CO₂CH(CH₃)₂ C═O Ia1.278 CH═CH CO₂CH₂CH(CH₃)₂ C═O Ia1.279 CH═CH CO₂CH₂CH₂F C═O Ia1.280 CH═CH CO₂CH₂CH₂Cl C═O Ia1.281 CH═CH CO₂CH₂CF₃ C═O Ia1.282 CH═CH CO₂CH₂CCl₃ C═O Ia1.283 CH═CH CO₂C₆H₅ C═O Ia1.284 CH═CH furan-2-yl C═O Ia1.285 CH═CH thien-2-yl C═O

Most preference is furthermore given to the following thiochromanoylpyrazolone derivatives of the formula I:

the compounds of the formula Ia2, in particular the compounds Ia2.1 to Ia2.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁸ is ethyl.

The compounds of the formula Ia3, in particular the compounds Ia3.1 to Ia3.285, which differ from the compounds Ia1.1 to Ia1.285 in that R⁸ is propyl.

The compounds of the formula Ia4, in particular the compounds Ia4.1 to Ia4.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁹ is methyl.

The compounds of the formula Ia5, in particular the compounds Ia5.1 to Ia5.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁸ is ethyl and R¹⁹ is methyl.

The compounds of the formula Ia6, in particular the compounds Ia6.1 to Ia6.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁸ is propyl and R¹⁹ is methyl.

The compounds of the formula Ia7, in particular the compounds Ia7.1 to Ia7.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is methylsulfonyloxy.

The compounds of the formula Ia8, in particular the compounds Ia8.1 to Ia8.285, which differ from the compounds Ia1.1 to Ia1.285 in that R17 is methylsulfonyloxy and R¹⁸ is ethyl.

The compounds of the formula Ia9, in particular the compounds Ia9.1 to Ia9.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is methylsulfonyloxy and R¹⁸ is propyl.

The compounds of the formula Ia10, in particular the compounds Ia10.1 to Ia10.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is methylsulfonyloxy and R¹⁹ is methyl.

The compounds of the formula Ia11, in particular the compounds Ia11.1 to Ia11.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is methylsulfonyloxy, R¹⁸ is ethyl and R¹⁹ is methyl.

The compounds of the formula Ia12, in particular the compounds Ia12.1 to Ia12.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is methylsulfonyloxy, R¹⁸ is propyl and R¹⁹ is methyl.

The compounds of the formula Ia13, in particular the compounds Ia13.1 to Ia13.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy.

The compounds of the formula Ia14, in particular the compounds Ia14.1 to Ia14.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy and R¹⁸ is ethyl.

The compounds of the formula Ia15, in particular the compounds Ia15.1 to Ia15.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy and R¹⁸ is propyl.

The compounds of the formula Ia16, in particular the compounds Ia16.1 to Ia16.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy and R¹⁹ is methyl.

The compounds of the formula Ia17, in particular the compounds Ia17.1 to Ia17.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy, R¹⁸ is ethyl and R¹⁹ is methyl.

The compounds of the formula Ia18, in particular the compounds Ia18.1 to Ia18.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylsulfonyloxy, R¹⁸ is propyl and R¹⁹ is methyl.

The compounds of the formula Ia19, in particular the compounds Ia19.1 to Ia19.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy.

The compounds of the formula Ia20, in particular the compounds Ia20.1 to Ia20.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy and R¹⁸ is ethyl.

The compounds of the formula Ia21, in particular the compounds Ia21.1 to Ia21.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy and R¹⁸ is propyl.

The compounds of the formula Ia22, in particular the compounds Ia22.1 to Ia22.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy and R¹⁸ is methyl.

The compounds of the formula Ia23, in particular the compounds Ia23.1 to Ia23.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy, R¹⁸ is ethyl and R¹⁹ is methyl.

The compounds of the formula Ia24, in particular the compounds Ia24.1 to Ia24.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is phenylcarbonylmethoxy, R¹⁸ is propyl and R¹⁹ is methyl.

The compounds of the formula Ia25, in particular the compounds Ia25.1 to Ia25.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy.

The compounds of the formula Ia26, in particular the compounds Ia26.1 to Ia26.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy and R¹⁸ is ethyl.

The compounds of the formula Ia27, in particular the compounds Ia27.1 to Ia27.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy and R¹⁸ is propyl.

The compounds of the formula Ia28, in particular the compounds Ia28.1 to Ia28.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy and R¹⁹ is methyl.

The compounds of the formula Ia29, in particular the compounds Ia29.1 to Ia29.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy, R¹⁸ is ethyl and R¹⁹ is methyl.

The compounds of the formula Ia30, in particular the compounds Ia30.1 to Ia30.285, which differ from the compounds Ia1.1 to Ia1.285 in that R¹⁷ is 4-methylphenylmethoxy, R¹⁸ is propyl and R¹⁹ is methyl.

The thiochromanoylpyrazolone derivatives of formula I can be obtained by various routes, for example by the following processes:

A. Preparation of compounds of the formula I where R¹⁷=hydroxyl by reacting an activated carboxylic acid IVa or a carboxylic acid IVb, which is preferably activated in situ, with a pyrazolone of the formula III to give the acylation product, followed by rearrangement.

L¹ represents a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.

The activated benzoic acid IVa can be employed directly, as in the case of the benzoyl halides, or generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. Here, the reactants and the auxiliary base are expediently employed in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on IVa or IVb, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkyl amines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

If the activated carboxylic acid component used is a benzoyl halide, it may be expedient to cool the reaction mixture to 0-10° C. during the addition of this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-500° C., until the reaction is complete. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude ester can be used for the rearrangement without any further purification.

The rearrangement of the esters to the compounds of the formula I is expediently carried out at 20-100° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Solvents which may be used are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in twice the equimolar ratio, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilylcyanide, for example in an amount of from 5 to 15, preferably approximately 10, mol percent, based on the ester.

Work-up can be carried out in a manner known per se. The reaction mixture is acidified, for example with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the precipitate which forms is filtered off with suction, and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

B. Preparation of compounds of the formula I where R¹⁷=halogen by reacting thiochromanoylpyrazolone derivatives of the formula I (where R¹⁷=hydroxyl) with halogenating agents:

Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionylchloride, oxalylchloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.

C. Preparation of compounds of the formula I where R¹⁷=OR²⁰, OSO₂R²¹, OPOR²²R²³ or OPSR²²R²³ by reacting thiochromanoylpyrazolone derivatives of the formula I (where R¹⁷=hydroxyl) with alkylating, sulfonylating or phosphonylating agents Vα, Vβ, Vγ or Vδ.

L² is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.

The compounds of the formula Vα, Vβ, Vγ or Vδ can be employed directly, such as, for example, in the case of the carbonyl halides, or generated in situ, for example activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide, etc.).

D. Preparation of compounds of the formula I where R¹⁷=OR²⁰, SR²⁰, POR²²R²³, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl by reacting compounds of the formula I where R¹⁷=halogen, OSO₂R²¹ with compounds of the formula VIα, VIβ, VIγ, VIδ, VIε or VIη, if appropriate in the presence of a base or with previous salt formation.

E. Preparation of compounds of the formula I where R¹⁷=SOR²¹, SO₂R²¹ by reacting compounds of the formula I where R¹⁷=SR²¹ with an oxidizing agent.

Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxy acetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.

For the reactions mentioned under points B to E, the following conditions apply:

The starting materials are usually employed in equimolar ratios. However, it may also be advantageous to use an excess of one component or the other.

If appropriate, it may be advantageous to carry out the reactions in the presence of a base. Here, the reactants and the base are expediently employed in equimolar amounts.

With respect to the processes C and D, it may, in certain cases, be advantageous to employ an excess of base, for example from 1.5 to 3 molar equivalents, in each case based on the starting material.

Suitable bases are tertiary alkyl amines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example, toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethylsulfoxide, or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is usually in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to give the product.

Depending on the reaction conditions, in the processes B to D the compounds Ia, Ib or mixtures of these may be formed. The latter can be separated by classic separation methods, such as, for example, crystallization, chromatography, etc.

F. Preparation of compounds of the formula I where R¹⁶=IIa by reacting a metallated pyrazole derivative of the formula VII with a carboxylic acid derivative of the formula IVa:

Here, M is a metal, in particular an alkali metal, such as lithium or sodium, an alkaline earth metal, such as, for example, magnesium, or a transition metal, such as palladium, nickel, etc. and L¹ is a nucleophilically replaceable leaving group such as halogen, for example chlorine or bromine, alkylsulfonate, such as mesylate, haloalkylsulfonate, such as triflate or cyanide.

The reaction is usually carried out at from −100° C. to the reflux temperature of the reaction mixture. Suitable solvents are inert aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran. The compounds of the formula IVa are usually employed in excess, but it may also be advantageous to employ them in equimolar amounts or in substoichiometric amounts. Work-up is carried out to give the product.

The metallated pyrazole derivatives of the formula VII can be formed in a manner known per se by reacting pyrazoles which are halogenated in 4-position with metals such as lithium, sodium, magnesium, etc., or with organometallic compounds, such as, for example, butyllithium. However, it is also possible to metallate pyrazoles which are linked to hydrogen in the 4-position directly, for example using the abovementioned metals or organometallic compounds. The reactions are usually carried out in an inert aprotic solvent, preferably in ethers, such as diethyl ether, tetrahydrofuran, etc. The reaction temperature is in the range from −100° C. to the boiling point of the reaction mixture. The compounds of the formula VII are usually directly reacted further or generated in situ.

The pyrazolones of the formula III used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001, J. Chem. Soc. 315, 383 (1997)).

The alkylating agents Vα, sulfonylating agents Vβ, phosphonylating agents Vγ or Vδ, and the compounds VIα, VIβ, VIγ, VIδ and VIε are likewise known, or they can be prepared analogously to known processes.

The carboxylic acid derivatives of the formula IV

where:

A is C₁-C₆-alkandiyl, C₂-C₆-alkenediyl, C₄-C₆-alkanedienediyl or C₂-C₆-alkynediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl;

R¹ is cyano, thiocyanato, nitro, OR⁴, SR⁵, SOR⁶, SO₂R⁶, ONR⁶R⁷, ON═CR⁶R⁸, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R³ is hydrogen, halogen or C₁-C₆-alkyl;

X is oxygen, sulfur, S═O, S(═O)₂, CR¹³R¹⁴, C═O or C═NR¹⁵;

m is 0, 1 or 2;

n is 0, 1, 2, 3 or 4;

R⁴, R⁵ are one of the radicals mentioned under R⁶;

are hydrogen, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, P(O)R¹¹R¹² or P(S)R¹¹R¹²;

are phenylcarbonyl, phenoxycarbonyl, phenyl-C₁-C₄-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C₁-C₄-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl or C₃-C₆-cycloalkyl, where the four above mentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl and C₁-C₄-haloalkoxycarbonyl;

is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where the phenyl and the heterocyclyl radical of the four last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R⁷ is hydrogen or C₁-C₆-alkyl;

R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, cyano or C₁-C₆-alkoxy;

R⁹ is one of the radicals mentioned under R⁴;

is C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, aminocarbonyl, N—C₁-C₆-alkylaminocarbonyl or N,N-di-(C₁-C₆-alkyl)aminocarbonyl;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkinyl;

R¹¹, R¹² are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl;

R¹³, R¹⁴ are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, N—C₁-C₆-alkylamino, N—C₁-C₆-haloalkylamino, N,N—(di-C₁-C₆-alkyl)amino, N—C₁-C₆-alkoxyamino, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;

or

R¹³, R¹⁴ together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R¹⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R²⁶ is hydroxyl or a radical which can be removed by hydrolysis;

are novel.

Examples of radicals which can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals which may be unsubstituted or substituted, halides, hetaryl radicals which are attached via nitrogen, amino and imino radicals which may be unsubstituted or substituted, etc.

Preference is given to carbonyl halides of the formula IVa where R²⁶=halogen

where the variables A, X, R¹ to R³, m and n are as defined under formula IV and

Hal is halogen, in particular chloride or bromide.

Likewise, preference is given to carboxylic acids of the formula IVb

where the variables A, X, R¹ to R³, m and n are as defined under formula IV.

Likewise, preference is given to carboxylic esters of the formula IVc

where the variables A, X, R¹ to R³, m and n are as defined under formula IV and

M is C₁-C₆-alkoxy.

The particularly preferred embodiments of the carboxylic acid derivatives of the formula IV with respect to the variables A, X, R¹ to R³, m and n correspond to those of the thiochromanoylpyrazolone derivatives of the formula I.

The carbonyl halides of the formula IVa (IV where R²⁶=Hal, in particular Cl, Br) can be prepared in a manner known per se (cf. L. G. Fieser, M. Fieser “Reagents for Organic Synthesis”, Vol. I, pp. 767-769 (1967)) by reacting the carboxylic acids of the formula IVb with halogenating reagents, such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride or oxalyl bromide.

The benzoic acids of the formula IVb can be prepared in a known manner by acidic or basic hydrolysis from the corresponding carboxylic esters IVc (IV where M═C₁-C₆-alkoxy) (J. March, “Advanced Organic Chemistry”, 4th Edition, p. 378 ff., Wiley-Interscience Publication, 1992).

The carboxylic esters of the formula IVc are obtainable by various routes, for example by one of the following processes:

1. Preparation of compounds of the formula IVc, especially where A═C₁-C₆-alkandiyl, in particular methanediyl, by reacting compounds of the formula VIII, where L³ is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, for example mesylate, haloalkylsulfonate, for example triflate, or cyanide,

with suitable nucleophiles HR¹ or phosphites, for example according to Arbuzow (J. March, “Advanced Organic Chemistry”, 4th Edition, p. 959, Wiley-Interscience Publication, 1992).

2. Preparation of compounds of the formula IVc where R¹=SOR⁶ or SO₂R⁶ by reacting compounds of the formula IVc where R¹=SR⁶ with an oxidizing agent.

Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.

3. Preparation of compounds of the formula IVc where R¹=P(S)R¹¹R¹² by reacting compounds of the formula IVc where R¹=P(O)R¹¹R¹² with sulfurizing agents, such as P₄S₁₀ (cf. I. W. Still et al., Can. J. Chem. 56, 1423 (1978)), Lawessons Reagent (cf. A. Shabana et al., Chem. Ind. (London) 15, 553 (1984)) or p-toluene disulfide (cf. K. Takuyuki et al., Chem. Lett. 501 (1986)).

4. Preparation of compounds of the formula IVc where A═C₂-C₆-alkandiyl, C₃-C₆-alkendiyl, C₃-C₆-alkynediyl, where the multiple bond is not conjugated to the phenyl ring, by reacting compounds of the formula VIII, where L₃ is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, for example mesylate or haloalkylsulfonate, for example triflate,

with a carbon nucleophile. Suitable for this purpose are, for example organometallic, such as Grignard, organolithium or organo zinc compounds, or CH-acidic compounds such as aldehydes, ketones, carboxylic acid derivatives (esters, amides, etc.), nitriles, sulfones, 1,3-dithio compounds, diketones, dicarboxylic ester derivatives, ketocarboxylic acid derivatives, dinitriles, ketonitriles, cyanocarboxylic acid derivatives or bisulfones.

If appropriate, it may be advantageous in the reaction with CH-acidic compounds to employ bases, such as alkali metal or alkaline earth metal hydroxides, for example sodium hydroxide or potassium hydroxide, alkali metal or alkaline earth metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal or alkaline earth metal bicarbonates, for example sodium bicarbonate or potassium bicarbonate, alkali metal or alkaline earth metal alkoxides, for example sodium methoxide, sodium ethoxide or potassium tert-butoxide, alkali metal or alkaline earth metal hydrides, for example sodium hydride, or organometallic bases, such as butyllithium.

5. Preparation of compounds of the formula IVc where A═C₂-C₆-alkendiyl, in particular where A═C₂-C₆-alkendiyl, where the double bond is conjugated to the phenyl ring, by reacting compounds of the formula VIII where L³=halogen, in particular bromine, with. triarylphosphines, such as triphenylphosphine, and subsequent reaction with appropriately substituted aldehydes or ketones in the presence of bases according to Wittig. Also suitable are related reactions, for example using phosphonates according to Horner-Emmons (cf. J. March, “Advanced Organic Chemistry, 4th Edition, p. 959 ff., Wiley-Interscience Publication, 1992).

By way of example, a Wittig reaction is shown below:

Furthermore, these products can be obtained by using the “inverse starting materials”, such as, for example

6. Preparation of compounds of the formula IVc where A═C₂-C₆-alkendiyl, in particular where A═C₂-C₆-alkendiyl, where the double bond is conjugated to the phenyl radical, by aldol reaction and related reactions in a manner known per se (cf. J. March, “Advanced Organic Chemistry”, 4th edition, p. 937, Wiley-Interscience Publication, 1992)

7. Preparation of compounds of the formula IVc where A═C₂-C₆-alkynediyl, in particular where A═C₂-C₆-alkindiyl, where the triple bond is conjugated to the phenyl ring, by dehalogenating compounds of the formula X using a base, such as alkali metal or alkaline earth metal hydroxides, for example potassium hydroxide, analogously to processes known from the literature (cf. L. I. Smith et al., Org. Synth. 22, 50 (1942); E. V. Dehmlow et al., Liebigs Ann. Chem. 1 (1980).)

The halide of the formula VIII, in particular where A=methanediyl, and L³=bromine, can be obtained by halogenating the corresponding alkyl compounds XI in the presence of a free radical initiator or by irradiation.

Suitable halogenating agents are, for example, chlorine, bromine, N-chloroamine, N-N-chlorosuccinimide, N-bromosuccinimide etc. Suitable free radical initiators are, inter alia, benzoylperoxide or azobisisobutyronitrile. However, it is also possible to carry out the reaction under irradiation with suitable radiation sources, such as UV-Hg low-pressure or Hg high-pressure lamps.

Furthermore, the halides of the formula VIII, in particular where A=methanediyl and L³=bromine, can be obtained by halogenating the corresponding alcohols XII.

Suitable halogenating agents are phosphorus pentachloride, phosphorus oxychloride, phosphorus oxybromide, thionyl chloride, thionyl bromide, phosgene, carbonyl bromide, oxalyl chloride, oxalyl bromide, and binary systems, such as carbon tetrachloride/triphenylphosphine or carbon tetrabromide/triphenylphosphine, etc.

The alkyl sulfonates or haloalkyl sulfonates of the formula VIII, in particular where A=methanediyl, are obtainable by reacting alcohols of the formula XII with activated alkyl- or haloalkylsulfonic acids, such as alkyl- or haloalkylsulfonic anhydrides or alkyl- or haloalkylsulfonic halides.

The aldehydes or ketones of the formula IX, in particular where A′=bond can be obtained by oxidizing appropriate compounds of the formlua XII in a manner known per se.

Suitable oxidizing agents are, inter alia, hydrogen peroxide, chromic acid, potassium permanganate, pryidinium dichromate, cerium ammonium nitrate, N-methylmorpholine N-oxide or tetramethylmorpholine N-oxide) cf. J. March, “Advanced Organic Chemistry”, 4th Edition, p. 1158 ff., Wiley-Interscience Publication, 1992).

The compounds of the formula X are prepared by halogenating the double bond of the compounds of the formula IVc where A═C₂-C₆-alkendiyl, analogously to processes known from the literature (cf. J. March, “Advanced Organic Chemistry”, 4th Edition, p. 812 ff., Wiley-Interscience Publication, 1992).

Suitable halogenating agents are, in particular, chlorine or bromine.

The alcohols of the formula XII can be obtained in a manner known per se by reacting appropriate aldehydes or ketones with carbon nucleophiles. Suitable carbon nucleophiles are, for example, organometallic reagents, such as Grignard reagents, organolithium or organotin compounds, but also hydrides (or reducing agents such as lithium aluminum hydride, boranate, etc. or “hydride generating systems”, such as reduction using hydrogen over a catalyst). This is described below by way of example.

The aldehyde of the formula XIII is obtainable by oxidizing compounds of the formula VIII where A=methanediyl and L³=chlorine, bromine, in particular bromine.

Suitable oxidizing agents are, inter alia, barium permanganate (Ba(MnO₄)₂; cf. H. Firouzabadi et al., Tetrahedron 46, 6869 (1990)), silver nitrate (AgNO₃; cf. E. Ghera et al., Synthesis 504 (1984)), potassium dichromate (K₂Cr₂O₇; cf. E. Santaniello, Tetrahedron Lett. 4581 (1979)), bis-(p-methoxyphenyl)selenium oxide (cf. K. Ariyoshi et al., Chem. Lett. 6, 891 (1984)) or isopropyl nitrite (cf. S. Kuriatkowski et al., Tetrahedron Lett. 2093 (1990)).

If appropriate, it may be advantageous in the synthesis variants described above to introduce protective groups for certain functionalities if the functionalities are not compatible with the reaction conditions required. The choice of protective groups depends both on the reaction conditions and on the molecular structure. Protective groups, their introduction and removal are generally known from the literature (cf. T. W. Greene et al., “Protective Groups in Organic Synthesis”, 2^(nd) Ed., Wiley-New York, 1991) and can be used analogously to processes known from the literature.

Furthermore, it may be necessary to carry out a combination of the synthesis variants described above.

Likewise, it is possible to introduce further substituents or to modify substituents that are already present, by electrophilic, nucleophilic, free-radical or organometallic reactions and also by oxidation or reduction reactions.

The reactions above are usually carried out at atmospheric pressure.

The reaction temperatures are generally between −100° C. and the reflux temperature of the reaction mixture.

In general, solvents or solvent mixtures are used which are suitable for the reaction conditions.

The starting materials are usually employed in stoichiometric amounts. However, it may also be advantageous to use less or more than the stoichiometric amount of one reactant or the other.

Furthermore, the synthesis of compounds of the formula XI (where X=S; m=0) below is novel:

In the literature, the synthesis of 5-methyl-2,3-dihydro-1,4-benzodithiine from the cyclic thioketal of 2-methyl-cyclohexanone using N-bromosuccinimide is described. However, the yield is below 50% (H. Tani et al., Heterocycles 36, 1783 (1993)).

It has now been found that the reaction of dithioketals of the formula XIV with a halogenating agent and subsequent treatment with a reducing agent gives satisfactory yields.

Suitable halogenating agents are, inter alia, N-bromosuccinimide, N-chlorosuccinimide, bromine or chlorine. They are generally employed in a three-fold excess, based on the starting materials. However, it may also be advantageous to employ a greater or smaller excess. Suitable solvents for the first step of this synthesis are, inter alia, inert solvents, such as halogenated hydrocarbons, for example dichloromethane, trichloromethane, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, etc. or aromatics, such as benzene, toluene or xylene. It may also be advantageous to use solvent mixtures. The reaction temperatures during the first step are generally from −80° C. to the reflux temperature of the reaction mixture. The reaction is preferably carried out at from −80° C. to room temperature, in particular at from −80° C. to 0° C.

Suitable reducing agents are alanates, such as lithium alanate, diisobutylaluminum hydride, boranates, such as sodium boranate, diborane, metal hydrides, such as trialkyltin hydride, metals, such as zinc, tin, etc. The reducing agent is generally employed in equimolar amounts. However, it may also be advantageous to use more or less than the stoichiometric amount. Suitable solvents for the second reaction step are, in particular, inert solvents, such as ethers, for example diethyl ether, methyl tert-butyl ether or 1,4-dioxane, or dipolar solvents, such as dimethylformamide, diethylformamide, dimethyl sulfoxide, N-methyl pyrrolidone. However, it is also possible to use alcohols, such as methanol, ethanol, etc. The reaction is generally carried out at from 0° C. to the reflux temperature of the reaction mixture, preferably at from 0 to 100° C., in particular at from 10 to 40° C.

The preparation of the compounds of the formula XIV from the corresponding cyclohexanone derivatives is carried out by reaction with dithiols, using methods known per se (Cf. T. W. Greene, et al. in “Protective Groups in Organic Synthesis”, 2nd Edition, pp. 201-203, Wiley, New York, 1991).

PREPARATION EXAMPLES 1. 4-{[4,4-Dimethyl-8-propoxymethyl-1,1-dioxothiochroman-7-yl]-carbonyl}-5-hydroxy-1-methylpyrazole (Compound 2.17)

Step a) Methyl 3-(3-methyl-2-butenylthio)-2-methylbenzoate

43.5 g (0.275 mol) of 3-methyl-2-butenyl bromide were added dropwise to 50 g (0.275 mol) of methyl 3-thio-2-methyl-benzoate, and 37.9 g (0.275 mol) of potassium carbonate in 250 ml of acetone, and the mixture was stirred at room temperature overnight. The solvent was removed, the residue was taken up in water/ethyl acetate and the organic phase was dried and concentrated to dryness.

Yield: 67.9 g (99%); ¹H-NMR (CDCl₃): δ (in ppm)=7.63 (d, 1H); 7.41 (d, 1H); 7.16 (t, 1H); 5.25 (m, 1H); 3.90 (s, 3H); 3.49 (d, 2H); 2.60 (s, 3H); 1.70 (s, 3H); 1.56 (s, 3H).

Step b) Methyl 4,4,8-trimethylthiochromane-7-carboxylate

At −5 to 0° C., 206.4 g (1.09 mol) of titanium tetrachloride in 600 ml of methylene chloride were added dropwise to 67.9 g (0.27 mol) of methyl 3-(3-methyl-2-butenylthio)-2-methyl-benzoate in 600 ml of methylene chloride and the mixture was subsequently stirred at 0° C. for 3 hours. The reaction mixture was then poured into a mixture of 1.5 kg of ice and 500 ml of saturated ammonium chloride solution, and the phases that formed were separated. The organic phase was dried and the solvent was removed. The resulting orange oil (62.9 g) was used directly for the next step. For characterization, a sample was chromatographed over silica gel using ethyl acetate/cyclohexane (1:10). Melting point: 63° C.

Step c) Methyl 4,4,8-trimethyl-1,1-dioxothiochromane-7-carboxylate

30.7 g (0.12 mol) of methyl 4,4,8-trimethylthiochromane-7-carboxylate and a spatula tip of sodium tungstate were dissolved in 400 ml of glacial acetic acid and, at 50° C., 31.7 g (0.28 mol) of 30% strength hydrogen peroxide were added dropwise. The mixture was stirred at this temperature for another 5 hours and subsequently poured into ice water. The precipitated crystals were filtered off with suction, washed with water and dried. Yield: 31.8 g (91%); Melting point: 151° C.

Step d) Methyl 4,4-dimethyl-8-bromomethyl-1,1-dioxothiochromane-7-carboxylate

A little at a time, 20.5 g (0.12 mol) of N-bromosuccinimide were added with UV irradiation to a solution of 31 g (0.11 mol) of methyl 4,4,8-trimethyl-1,1-dioxothiochromane-7-carboxylate in 300 ml of acetonitrile at reflux temperature. At this temperature and under UV light, the mixture was stirred for another 1.5 hours and then poured into ice water. The residue was filtered off with suction, washed with water and dried.

Yield: 36.4 g (92%); Melting point: 163-165° C.

Step e): Propyl 4,4-dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylate (compound 3.12)

0.38 g (16.6 mmol) of sodium was added to 50 ml of propanol. After a clear solution had formed, 5.0 g (13.7 mmol) of methyl 4,4-dimethyl-8-bromomethyl-1,1-dioxothiochromane-7-carboxylate were added, and the mixture was stirred under reflux for 5 hours. After cooling, the solvent was distilled off and the residue was taken up in a 1:2 mixture of ethyl acetate and water. The organic phase was separated off, dried and concentrated.

Yield: 4.2 g; Melting point: 122-124° C.

Step f): 4,4-Dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylic acid (compound 3.13)

0.64 g (15.9 mmol) of sodium hydroxide was added to a solution of 3.9 g (10.6 mmol) of propyl 4,4-dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylate in a methanol/water mixture, and the reaction mixture was heated under reflux for 4 hours. After cooling, the organic solvent was removed and the residue was taken up in water and acidified with 2N hydrochloric acid. The precipitate that formed was filtered off with suction and dried.

Yield: 3.1 g; ¹H-NMR (d⁶-DMSO): δ (in ppm)=7.65 (s, 2H); 5.02 (s, 2H); 3.58 (m, 2H); 3.32 (m, 2H); 2.24 (m, 2H); 1.46 (q, 2H); 1.38 (s, 6H); 0.84 (t, 3H).

Step g): 4-{(4,4-Dimethyl-8-propoxymethyl-1,1-dioxothiochroman-7-yl)carbonyl}-5-hydroxy-1-methylpyrazole (compound 5 2.17)

A solution of 0.6 g (1.84 mmol) of 4,4-dimethyl-8-propoxymethyl-1,1-dioxothiochromane-7-carboxylic acid, 0.18 g (1.84 mmol) of 1-methyl-5-hydroxypyrazole and 0.38 g (1.84 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of acetonitrile was stirred at room temperature for 12 hours. The reaction mixture was subsequently stirred into a mixture of ethyl acetate and 2% strength aqueous sodium carbonate solution, and the precipitate which formed was filtered off with suction. The organic phase of the filtrate was dried and the solvent was distilled off. The resulting residue was dissolved in 5 ml of 1,4-dioxane, 0.51 g (3.7 mmol) of potassium carbonate were added and the mixture was heated under reflux for 4 hours. After cooling, the reaction mixture was taken up in ethyl acetate/water, and the aqueous phase was adjusted to pH 3 using 2N hydrochloric acid and subsequently extracted with ethyl acetate. The extract was dried and the solvent was removed, giving a solid.

Yield: 0.50 g; Melting point: 84° C.

2. 5-Methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylic acid (compound 3.31)

Step a) 6-methoxycarbonyl-5-methyl-1,4-dithia-spiro[4,5]-decane

Initially 41.0 g (436 mmol) of 1,2-dimercaptoethane and then 6.8 ml of boron trifluoride etherate were added dropwise to a solution of 49.4 g (291 mmol) of methyl 2-methyl-3-oxocyclohexanecarboxylate (prepared according to Gupla et al., J. Sci. Ind. Res. B, 1962, 21, 219) in 200 ml methylene chloride, and the mixture was stirred at room temperature overnight. 200 ml of 2N aqueous sodium hydroxide solution were added, the phases were separated, the organic phase was dried over sodium sulfate and the solvent was removed.

Yield: 56.7 g (yellow oil).

Step b) Methyl 5-methyl-2,3-dihydro-1,4-benzodithiine-6-carboxylate

At −78° C., 177.59 g (982 mmol) of N-bromosuccinimide were added to 80.5 g (327 mmol) of 6-methoxycarbonyl-5-methyl-1,4-dithia-spiro[4,5]-decane in 1200 ml of methylene chloride, and the mixture was stirred at this temperature for 30 minutes. The mixture was allowed to warm to room temperature and filtered through silica gel. The filtrate was washed successively with 10% strength sodium bicarbonate solution and 10% strength sodium hydrogen sulfite solution, dried over sodium sulfate and concentrated. The residue was subsequently dissolved in 500 ml of dimethylsulfoxide and added dropwise to 14.8 g (390 mmol) of sodium boranate in 200 ml of dimethylsulfoxide. The mixture was stirred for 3 hours, and 100 ml of water were then added dropwise. The mixture was extracted with ethyl acetate and dried over sodium sulfate, and the solvent was removed.

Yield: 54.5 g (yellow oil); ¹H-NMR(CDCl₃): δ (in ppm)=7.45 (d, 1H); 7.05 (d, 1H); 3.84 (s, 3H); 3.37-3.20 (m, 4H); 2.52 (s, 3H).

Step c) Methyl 5-methyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate

At 50-60° C., 208 g (1830 mmol) of a 30% strength hydrogen peroxide solution were added dropwise to 100 g (420 mmol) of methyl 5-methyl-2,3-dihydro-1,4-benzodithiine-6-carboxylate in 500 ml of glacial acetic acid and a spatula tip of sodium tungstate, and the mixture was stirred at 50° C. for 3 hours. The mixture was then poured into water and the resulting precipitate was filtered off with suction. The product was washed successively with sodium bisulfite solution and water and dried under reduced pressure.

Yield: 123 g (colorless solid); ¹H-NMR (d⁶-DMSO): δ (in ppm)=8.10 (d, 1H); 8.04 (d, 1H); 4.42 (m, 4H); 3.90 (s, 3H); 2.75 (s, 3H).

Step d) Methyl 5-bromomethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate

Under reflux and with UV irradiation, 12.9 g (73 mmol) of N-bromosuccinimide were added a little at a time to a suspension of 21 g (69 mmol) of methyl 5-methyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate in 200 ml of acetonitrile. After another 6 hours under the abovementioned conditions, the solvent was removed, the residue was stirred with water and the precipitate was filtered off with suction and dried.

Yield: 24.3 g; Melting point: 188° C. (with decomposition).

Step e) Methyl 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydrobenzodithiin-6-carboxylate (compound 3.30)

At room temperature, 2.35 g (13 mmol) of sodium methoxide in methanol (30% strength solution) were added dropwise to a solution of 5.0 g (13 mmol) of methyl 5-bromomethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylate in 50 ml of methanol, and the mixture was subsequently heated to 40° C. After 30 minutes, the solvent was removed, the residue was stirred with water and the aqueous phase was extracted with ethyl acetate. The solvent was removed and the residue was then chromatographed over silica gel.

Yield: 1.4 g (colorless solid); ¹H-NMR(CDCl₃): δ (in ppm)=8.40 (d, 1H); 8.08 (d, 1H); 6.25 (d, 1H); 6.07 (d, 1H); 4.02 (s, 3H); 3.94-3.42 (m, 4H); 3.18 (s, 3H).

Step f) 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-1,4-benzodithiine-6-carboxylic acid (compound 3.31)

A solution of 1.3 g (3.9 mmol) of methyl 5-methoxymethyl-1,1,4,4-tetraoxo-2,3-dihydro-benzodithiine-6-carboxylate in a 1:1 mixture of methanol/water was mixed with 0.23 g (5.8 mmol) of sodium hydroxide and heated under reflux for 1 hour. The solvent was removed and the residue was taken up in water and acidified with 2N hydrochloric acid. The resulting crystalline precipitate was filtered off with suction and dried.

Yield: 0.8 g (colorless solid); ¹H-NMR(d⁶-DMSO): δ (in ppm)=8.40 (d, 1H); 8.18 (d, 1H); 6.18 (d, 1H); 6.08 (d, 1H); 3.80-3.60 (m, 4H); 3.02 (s, 3H).

In addition to the abovementioned thiochromanoylpyrazolone derivative of the formula I and the carboxylic acid derivatives of the formula IV, other compounds which were prepared and are preparable in an analogous manner are listed in Tables 2 and 3 below:

TABLE 2 Ia

Ia (where A = CH₂, R³, R¹⁹ = H, m = 2, n = 0) No. R¹ X R¹⁷ R¹⁸ m.p. [° C.] 2.1 SCH₃ C(CH₃)₂ OH CH₃ 233 2.2 SCH₃ C(CH₃)₂ OH CH₂CH₃ 205 2.3 SO₂CH₃ C(CH₃)₂ OH CH₃ 196-197 2.4 SO₂CH₃ C(CH₃)₂ OH CH₂CH₃ 173-175 2.5 S(CH₂)₂CH₃ C(CH₃)₂ OH CH₃ 187-188 2.6 S(CH₂)₂CH₃ C(CH₃)₂ OH CH₂CH₃ 163 2.7 SO(CH₂)₂CH₃ C(CH₃)₂ OH CH₃ 250 2.8 SO(CH₂)₂CH₃ C(CH₃)₂ OH CH₂CH₃ 250 2.9 SCH(CH₃)₂ C(CH₃)₂ OH CH₃ 163-165 2.10 SCH(CH₃)₂ C(CH₃)₂ OH CH₂CH₃ 163-165 2.11 SO₂CH(CH₃)₂ C(CH₃)₂ OH CH₃ 125-127 2.12 SO₂CH(CH₃)₂ C(CH₃)₂ OH CH₂CH₃ 96-98 2.13 S-(benz- C(CH₃)₂ OH CH₃ 215 thiazol-2-yl) 2.14 S-(benz- C(CH₃)₂ OH CH₂CH₃ 288 thiazol-2-yl) (decomp.) 2.15 OCH₃ C(CH₃)₂ OH CH₃ >250 2.16 OCH₃ C(CH₃)₂ OH CH₂CH₃ 222-223 2.17 O(CH₂)₂CH₃ C(CH₃)₂ OH CH₃ 84 2.18 O(CH₂)₂CH₃ C(CH₃)₂ OH CH₂CH₃ 154-156 2.19 P(O)(OCH₂CH₃)₂ C(CH₃)₂ OH CH₃ 183-185 2.20 SO₂(CH₂)₃CH₃ C(CH₃)₂ OH CH₃ 101-104 2.21 SO₂(CH₂)₃CH₃ C(CH₃)₂ OH CH₂CH₃ 89-91 2.22 SO₂CH₂CH₃ C(CH₃)₂ OH CH₃ 177 2.23 SO₂CH₂CH₃ C(CH₃)₂ OH CH₂CH₃ 194-197 2.24 OCH₂CF₃ C(CH₃)₂ OH CH₃ 185-187 2.25 OCH₂CF₃ C(CH₃)₂ OH CH₂CH₃ 178 2.26 OCH₂CH₂F C(CH₃)₂ OH CH₃ 194-195 2.27 OCH₂CH₂F C(CH₃)₂ OH CH₂CH₃ 184-185

TABLE 3 III

(where A = CH₂, R³ = H, m = 2, n = 0) m.p. [° C.] or ¹H-NMR No. R¹ M X [δ in ppm] 3.1 SCH₃ OCH₃ C(CH₃)₂ 7.80(d, 1H); 7.40 (d, 1H); 4.68(s, 2H); 3.91(s, 3H); 3.45(m, 2H); 2.35 (m, 2H); 2.08(s, 3H); 1.43(s, 6H); 3.2 SCH₃ OH C(CH₃)₂ 7.84(d, 1H); 7.64 (d, 1H); 4.58(s, 2H); 3.60(m, 2H); 2.22(m, 2H); 1.96 (s, 3H); 1.38(s, 6H); 3.3 SO₂CH₃ OH C(CH₃)₂ 223 3.4 S(CH₂)₂CH₃ OCH₃ C(CH₃)₂ 87 3.5 S(CH₂)₂CH₃ OH C(CH₃)₂ 163-166 3.6 SO₂(CH₂)₂CH₃ OH C(CH₃)₂ 158-160 3.7 SCH(CH₃)₂ OCH₃ C(CH₃)₂ 79-80 3.8 SCH(CH₃)₂ OH C(CH₃)₂ 191-192 3.9 SO₂CH(CH₃)₂ OH C(CH₃)₂ 239-240 3.10 OCH₃ OCH₃ C(CH₃)₂ 131-133 3.11 OCH₃ OH C(CH₃)₂ 227-229 3.12 O(CH₂)₂CH₃ O(CH₂)₂CH₃ C(CH₃)₂ 7.66(d, 1H); 7.42 (s, 1H); 5.20(s, 2H); 4.24(t, 2H); 3.40(m, 4H); 2.36 (m, 2H)1.78(m, 2H); 1.53(m, 2H); 1.40(s, 6H); 1.00 (t, 3H); 0.85(t, 3H); 3.13 O(CH₂)₂CH₃ OH C(CH₃)₂ 145 3.14 pyrazol-1-yl OCH₃ C(CH₃)₂ 171 3.15 pyrazol-1-yl OH C(CH₃)₂ 179 3.16 1,2,4-triazol-1-yl OCH₃ C(CH₃)₂ 8.26(s, 1H); 7.90 (d, 1H); 7.85(s, 1H); 7.55(d, 1H); 6.33(s, 2H); 3.92 (s, 3H); 3.52(m, 2H); 2.38(m, 2H); 1.46(s, 6H); 3.17 1,2,4-triazol-1-yl OH C(CH₃)₂ 265 3.18 morpholin-4-yl OCH₃ C(CH₃)₂ 208-210 3.19 morpholin-4-yl OH C(CH₃)₂ 224 3.20 S-benzthiazol-2-yl OCH₃ C(CH₃)₂ 137-138 3.21 S-benzthiazol-2-yl OH C(CH₃)₂ 108-109 3.22 P(O)(OCH₂CH₃)₂ OCH₃ C(CH₃)₂ 7.89(d, 1H); 7.40 (d, 1H); 4.50(d, 2H); 4.12(m, 2H); 4.06(m, 2H); 3.97 (s, 3H); 3.42(m, 2H); 2.38(m, 2H); 1.42(s, 6H); 1.24 (t, 6H); 3.23 P(O)(OCH₂CH₃)₂ OH C(CH₃)₂ 139-142 3.24 SCH₂CH₃ OCH₃ C(CH₃)₂ 128-137 3.25 SCH₂CH₃ OH C(CH₃)₂ 205-208 3.26 S(CH₂)₃CH₃ OCH₃ C(CH₃)₂ 7.80(d, 1H); 7.38 (d, 1H); 4.68(s, 2H); 3.90(s, 3H); 3.44(m, 2H); 2.56 (t, 2H); 2.36(m, 2H); 1.40(m, 10H); 0.85(t, 3H); 3.27 SO₂CH₂CH₃ OH C(CH₃)₂ 230 3.28 S(CH₂)₃CH₃ OH C(CH₃)₂ 81-83 3.29 SO₂(CH₂)₃CH₃ OH C(CH₃)₂ 180-182 3.30 OCH₃ OCH₃ SO₂ 8.40(d, 1H); 8.08 (d, 1H); 6.25(d, 1H); 4.02(s, 3H); 3.94-3.42(m, 4H), 3.18(s, 3H); 3.31 OCH₃ OH SO₂ 8.40(d, 1H); 8.18 (d, 1H); 6.18(d, 1H); 6.08(d, 1H); 3.80-3.60(m, 4H); 3.02(s, 3H); 3.32 N(CH₃)(COCF₃) OH C(CH₃)₂ 203-205 3.33 N(CH₃)(COCF₃) OCH₃ C(CH₃)₂ 140-143 3.34 OCH₂CH₂F OH C(CH₃)₂ 167-168 3.35 OCH₂CH₂F OCH₃ C(CH₃)₂ 101(decomp.) 3.36 NO₂ OCH₃ C(CH₃)₂ 154-157 3.37 SO₂CH₂CH═CH₂ OH C(CH₃)₂ 63 3.38 SCH₂CH═CH₂ OH C(CH₃)₂ 170-173 3.39 SCH₂CH═CH₂ OCH₃ C(CH₃)₂ 134 3.40 OCH₂CF₃ OH C(CH₃)₂ 184-186 3.41 OCH₂CF₃ OCH₃ C(CH₃)₂ 94-95 3.42 OCH(CH₃)₂ OH C(CH₃)₂ 142-144 3.43 S-(1,2,3- OCH₃ C(CH₃)₂ 59 triazol-5-yl) 3.44 N(CH₂CH═CH₂)₂ OH C(CH₃)₂ 85 3.45 N(CH₂CH═CH₂)₂ OCH₃ C(CH₃)₂ 69 3.46 N(CH₃) OCH₃ C(CH₃)₂ 116 3.47 N(CH₂CH₂CH₃)₂ OCH₃ C(CH₃)₂ 7.50(d, 1H); 7.36 (d, 1H); 4.24(s, 2H); 3.80(s, 3H); 3.40(m, 2H); 2.35 (m, 6H); 1.40(s, 6H); 0.76(t, 6H); 3.48 S(CH₂)₂CH₃ OH C═O 142-144 3.49 SCH₃ OCH₃ C═O 117-118

The compounds of the formula I and their agriculturally useful salts are suitable for use as herbicides, both in the form of isomer mixtures and in the form of the pure isomers. The herbicidal compositions which comprise compounds of the formula I effect very good control of vegetation on non-crop areas, especially at high rates of application. In crops such as wheat, rice, maize, soya and cotton, they act against weeds and grass weeds without inflicting substantial damage to the crop plants. This effect is observed mainly at low rates of application.

Depending on the application method in question, the compounds of the formula I, or herbicidal compositions comprising them, can also be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I can also be used in crops which, by means of breeding, including genetic engineering methods, have been made tolerant to the action of herbicides.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries which are customary for the formulation of crop protection agents.

Suitable inert auxiliaries are essentially:

mineral oil fractions of medium to high boiling point such as kerosine and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the thiochromanoylpyrazolone derivatives of the formula I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and these concentrates are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, of alkyl- and alkylarylsulfonates, of alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise approximately from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (in accordance with NMR spectra).

The formulation examples which follow illustrate the preparation of such products:

I. 20 parts by weight of compound No. 2.1 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound No. 2.3 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound No. 2.7 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound No. 2.16 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

V. 3 parts by weight of compound No. 2.23 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active ingredient.

VI. 20 parts by weight of compound No. 2.24 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of compound No. 2.19 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of compound No. 2.15 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I, or the herbicidal compositions, may be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come in as little contact as possible, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil surface (post-directed, lay-by).

Depending on the control target, the season, the target plants and the growth stage, the rates of application of compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active substance (a.s.) per ha.

To widen the spectrum of action and to achieve synergistic effects, the thiochromanoylpyrazolone derivatives of the formula I may be mixed with a large number of representatives of other groups of herbicidal or growth-regulating active ingredients and applied jointly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

Furthermore, it may be advantageous to apply the compounds of the formula I, alone or in combination with other herbicides, also as a mixture with other crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for remedying nutritional and trace-element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.

USE EXAMPLES

The herbicidal activity of the thiochromanoylpyrazolone derivatives of the formula I was demonstrated by the following greenhouse experiments:

the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

In the case of the pre-emergence treatment, the active ingredients, which were suspended or emulsified in water, were planted directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.25 or 0.125 kg of a.s. (active substance) per ha.

Depending on the species, the plants were kept at from 10 to 25° C. or from 20 to 35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments belonged to the following species:

Scientific Name Common name Avena fatua wild oat Echinocloa crus-gali common barnyard-grass Chenopodium album lambsquarter Ipomoea ssp. morning glory Polygonum persicaria redshank Setaria viridis bottlegrass Sinapis alba white mustard Solanum nigrum black nightshade Triticum aestivum spring wheat Veronica ssp. speadwell

At application rates of 0.25 or 0.125 kg/ha, the compound 2.3 had very good post-emergence activity against the harmful plants Echinocloa crus-gali, Ipomoea spp., Solanum nigrum and Veronica ssp., and it was at the same time compatible with the crop plant Triticum aestivum. Furthermore, the compound 2.17 had very good activity against the weeds Avena fatua, Setaria viridis, Polygonum persicaria and Sinapis alba. 

We claim:
 1. A thiochromanoylpyrazolone derivative of the formula I:

where: A is C₁-C₆-alkanediyl, C₂-C₆-alkenediyl, C₄-C₆-alkadienediyl or C₂-C₆-alkynediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl; R¹ is cyano, thiocyanato, nitro, OR⁴, SR⁵, SOR⁶, SO₂R⁶, ONR⁶R⁷, ON=CR⁶R⁸, NR⁹R¹⁰, P(O)R¹¹R¹², P(S)R¹¹R¹², COR⁶, CO₂R⁶, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R³ is hydrogen, halogen or C₁-C₆-alkyl; X is oxygen, sulfur, S═O, S(═O)₂, CR¹³R¹⁴, C═O or C═NR¹⁵; m is 0, 1 or 2; n is 0, 1, 2, 3 or 4; R⁴, R⁵ are one of the radicals mentioned under R⁶; are hydrogen, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, P(O)R¹¹R¹² or P(S)R¹¹R¹²; are phenylcarbonyl, phenoxycarbonyl, phenyl-C₁-C₄-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C₁-C₄-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R⁶ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl or C₃-C₆-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl and C₁-C₄-haloalkoxycarbonyl; is phenyl, phenyl-C₁-C₄-alkyl, heterocyclyl or heterocyclyl-C₁-C₄-alkyl, where the phenyl and the heterocyclyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R⁷ is hydrogen or C₁-C₆-alkyl; R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, cyano or C₁-C₆-alkoxy; R⁹ is one of the radicals mentioned under R⁴; is C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, aminocarbonyl, N—C₁-C₆-alkylaminocarbonyl or N,N-di-(C₁-C₆-alkyl)aminocarbonyl; R¹⁰ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkinyl; R¹¹, R¹² are hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R¹³, R¹⁴ are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, N—C₁-C₆-alkylamino, N—C₁-C₆-haloalkylamino, N,N—(di-C₁-C₆-alkyl)amino, N—C₁-C₆-alkoxyamino, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl; or R¹³, R¹⁴ together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹⁶ is a radical IIa or IIb,

where: R¹⁷ is hydroxyl, mercapto, halogen, OR²⁰, SR²⁰, SOR²¹, SO₂R²¹, OSO₂R²¹, P(O)R²²R²³, OP(O)R²²R²³, P(S)R²²R²³, OP(S)R²²R²³, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R¹⁹ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-haloalkylthio; R²⁰ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkinyl, C₃-C₆-haloalkinyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkinylcarbonyl, C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkinyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkinylaminocarbonyl, N,N-di-(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkinyl)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₁-C₆-alkoxy)—N—(C₁-C₆-alkyl)aminocarbonyl, N—(C₃-C₆-alkenyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, N—(C₃-C₆-alkinyl)—N—(C₁-C₆-alkoxy)aminocarbonyl, di-(C₁-C₆-alkyl)aminothiocarbonyl or C₁-C₆-alkoxyimino-C₁-C₆-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl, hydroxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁-C₄-alkylcarbonyloxy or C₃-C₆-cycloalkyl; is phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C₁-C₆-alkyl)—N—(phenyl)aminocarbonyl, phenyl-C₂-C₆-alkenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C₁-C₆-alkyl)—N—(heterocyclyl)aminocarbonyl or heterocyclyl-C₂-C₆-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²¹ is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl or C₃-C₆-cycloalkyl, where the four abovementioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl; is phenyl, phenyl-C₁-C₆-alkyl, heterocyclyl or heterocyclyl-C₁-C₆-alkyl, where the phenyl and the heterocyclyl radical of the last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R²², R²³ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, phenyl, phenyl-C₁-C₄-alkyl or phenoxy, where the three last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or C₁-C₄-alkoxycarbonyl; R²⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkinyl, C₃-C₆-haloalkinyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl, hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, amino, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino or C₁-C₆-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl or C₃-C₆-cycloalkyl; is phenyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C₁-C₄-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁵ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkinyl; and its agriculturally useful salts.
 2. A process for preparing compounds of the formula I where R¹⁷=hydroxyl, as claimed in claim 1, which comprises acylating a pyrazolone of the formula III;

where the variables R¹⁸ and R¹⁹ are as defined in claim 1 with an activated carboxylic acid IVa or a carboxylic acid IVb

where the variables R¹ to R³, A, X, m and n are as defined under claim 1 and L¹ is a nucleophilically replaceable leaving group, and rearranging the acylation product, if appropriate in the presence of a catalyst, to give the compounds I where R¹⁷=hydroxyl.
 3. A process for preparing compounds of the formula I as claimed in claim 1 where R¹⁷=halogen, which comprises reacting a thiochromanoylpyrazolone derivative of the formula I where R¹⁷=hydroxyl with a halogenating agent.
 4. A process for preparing compounds of the formula I as claimed in claim 1 where R¹⁷=OR²⁰, OSO₂R²¹, OP(O)R²²R²³ or OP(S)R²²R²³, which comprises reacting a thiochromanoylpyrazolone derivative of the formula I where R¹⁷=hydroxyl with an alkylating agent Vα, sulfonylating agent Vβ or phosphonylating agent Vγ or Vδ, L²—R²⁰ L²—SO₂R²¹ L²—P(O)R²²R²³ L²—P(S)R²²R²³ Vα Vβ Vγ Vδ

where the variables R²⁰ to R²³ are as defined in claim 1 and L² is a nucleophilically replaceable leaving group.
 5. A process for preparing compounds of the formula I as claimed in claim 1 where R¹⁷=OR²⁰, SR²⁰, P(O)R²²R²³, NR²⁴R²⁵, ONR²¹R²¹ or N-bonded heterocyclyl, which comprises reacting a thiochromanoylpyrazolone derivative of the formula I where R¹⁷=halogen or OSO₂R²¹ with a compound of the formula VIα, VIβ, VIγ, VIδ, VIε or VIη HOR²⁰ HSR²⁰ HPOR²²R²³ HNR²⁴R²⁵ HONR²¹R²¹ VIα VIβ VIγ VIδ VIε H(N-bonded heterocyclyl) VIη

where the variables R²⁰ to R²⁵ are as defined in claim 1, if appropriate in the presence of a base.
 6. A process for preparing compounds of the formula I as claimed in claim 1 where R¹⁷=SOR²¹, SO₂R²¹, which comprises reacting a compound of the formula I where R¹⁷=SR²¹ with an oxidizing agent.
 7. A process for preparing compounds of the formula I where R¹⁶=IIa as claimed in claim 1, which comprises reacting a metallated pyrazole derivative of the formula VII where M is a metal and R¹⁷ to R¹⁹ are as defined in claim 1 with a carboxylic acid derivative of the formula IVa where R¹ to R³, A, X, m and n are as defined in claim 1 and L¹ represents a nucleophilically replaceable leaving group


8. A composition, comprising a herbicidally effective amount of at least one thiochromanoylpyrazolone derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1, and auxiliaries which are customarily used for formulating crop protection agents.
 9. A process for preparing compositions as claimed in claim 8, which comprises mixing a herbicidally effective amount of at least one thiochromanoylpyrazolone derivative of the formula I or an agriculturally useful salt of I and auxiliaries which are customarily used for formulating crop protection agents.
 10. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one thiochromanoylpyrazolone derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 to act on plants, their habitat and/or on seeds. 